Mercury derivatives of phthalein and method of preparing same



} Vpht alein by. carbon dionid,

halingeriecormtaining specification andclaims to inc Patented Aug. 18, 111-925.

\ haircare-es PATENT,

nnwm 0. warm, or nnmmonn, MARYLAND. 1 Reasons nsnrvarrvrs or rn'rrmmm AND METHOD or rial-rename same.

m a ea Application filed my 26, 1921, Serial No. 487,685. Renewed January 5, mac.

To all who at it may concern."

Be .it lmown that I. EDWIN 0. WHITE,

a citizen of the United States, residing at Baltimore, in the State of Maryland, have invented certain new and useful Improvements Mercury Derivatives of Phthaleins and Methods of Preparing Same, of which the following is a specification.

It is known that by the action of mercuric chlorid or other soluble salts] of mercury in excess on solutions of salts of phthaleins, di-merou prepared, such (ii-derivatives being the ex- .clusivehproducts or the reaction. If mercuric c orid he used the resulting products Hg Cl m; 0!.

each mercury atom being bound to carbon by one valence and to chlorin by the other.

The present invention relates to halogenfree mono-mercury derivatives of phthaleins, in which, it is believed,-the.mercury is bound by one valence to carbon and by the other to a hydroxyl, group. Such compounds are 'decidedl lam toxlc than the erivatives previously described. I

My novel compounds may be prepared by boiling the solution of a soluble salt, usually a sodium salt, at a phthalein with the molecular equivalent of freshly precipitated yel-- low end of mercury until the latter is dissolved; freeing the solution of any traces of mercury or mercurous oxid which may have been formed; and'then evaporating the clear solution to dryness, preferably under reduced pressure to avoid overheating.

In the specific case of phenolphthalein the solution of the 'rnerourated salt is unstable; it is therefore regarded as preferable to recipitate the free mercurated, phenoL and to filter, dprecipitate, which may wash and dry the by means of sodium then be ro -dissolve hydroxid.

The term phthalein is employed in the ude not only non-substituted phthalcins, but such substltuted phtha'leins as hat/eat least one free position ortho'to the phencl-hydroxyl group, or tothe quinone gran in case the phthalein exists in the quinoi or colored modifica derivatives can be.

tion; such for example as phenol hthalein; .ortho cresolphtha ein, thymol fluorescein, methyl fiuorescein, gallein, phenolsulfonphthalein,

Exam Ze l.-3.18 grams of phenolphthal ein are issolved in 25 c. c. of normal sodium hydroxid solution, diluted to 150 c. o'., and boiled with 2.16 grams of freshly precipitated yellow mercuric ox'id. for 3-4 hours. After removing the small amount of gra precipitate, the merourated .phenolphthalein is precipitated by carbon dioxid in the form of a purplish white, curd-like bed I This precipitate isthen re-dissolved in t e minimum tion,

Ewam Ze'll'. 20i c. c. of normal sodium hydroxi solution are heated with 3.5 grams of fiuorescein, which is slightly in excess of the amountthat will dissolve, thus precluding the presence of any excessalkali. After diluting to about 125 c. 0., 2.2 grams of phthalein,

cresolsulfonphthalem, thymolsulfonphthalein and the like.

proportion of-sodium hydroxid solu dryness, referably Emam/p'le [Hf-3.5 grams'of' phenolsulfonphthalein are dissolved in 10 c. c, of normal sodium hydroxid solution, diluted to about c. c.' and boiled with 2.2 grams of yellow mercuric oxid until the latter is dissolved. After remov ing the small amount offinely divided 'y'" precipitate, as in the previous exam is, the

This requires 4 to 6. hours.

solution is evaporated to dryness in t e same manner as inExampl II. The pmductis a dark reddish brown scale or powder, readsoluble in water. Before use of solutions I il of this substance forinjection, dilute sodium hydroxid is added until a distinct pur 1e color just appears. This provides a suite '18 degree of alkalinity."

The products prepared'as above are useful for purposes of injection as antisyphil-i itic agents. 1 Y I claiin:

1. The hereindescribed process r ing reacting with mercuric oxid in aqueous suspension on a soluble salt of a phthalein.

2. The hereindescribed process comprising reacting with mercuric oxid in aqueous suspension 0n the sodium salt of fluorescein.

3. The hereindescribed novel product having therapeutic properties, consisting essentially of a halogen-free alkali-metal salt of a mono-mercury derivative of a phthalein.

4:. The hereindescribed novel product having therapeutic properties, consisting essentially of a halogen-free alkali-metal salt of a mono-mercury derivative of fl'uorescein.

5. The hereindescribed process of preparing halogen-free mercury compounds of phthaleins which comprises mixing freshly precipitated oxid of mercury With a solution of a soluble salt of a phthalein and boiling the mixture.

In testimony whereof, I aflix my signature.

EDWIN C. WHITE. 

